Synthesis of a Bicyclic Piperazine from l-Aspartic Acid and Application of a Fluoride-Promoted SNAr Coupling

…, JD McKinley, DE Bourassa, JJ Teixeira…

Index: Sieser, Janice E.; Singer, Robert A.; McKinley, Jason D.; Bourassa, Dennis E.; Teixeira, John J.; Long, James Organic Process Research and Development, 2011 , vol. 15, # 6 p. 1328 - 1335

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Citation Number: 4

Abstract

The process development is reported of a pivotal C–N bond formation involving ((7 R, 9a S)- octahydro-1 H-pyrido [1, 2-a] pyrazin-7-yl) methanol (2) undergoing nucleophilic aromatic substitution with 3-chlorobenzo [d] isoxazole (3) to furnish ((7 R, 9a S)-2-(benzo [d] isoxazol- 3-yl) octahydro-1 H-pyrido [1, 2-a] pyrazin-7-yl) methanol (4) as a key intermediate for a family of compounds (1). Essential to the success of the coupling is the use of fluoride in ...